2-Methoxybenzaldehyde → N-[(2-methoxyphenyl)methylidene]hydroxylamine

HRID 1039183Notes

Reaction equation

HRID 1039183 reaction equation
[OH-:1].[Na+].[CH:3](=O)[C:4]1[C:5]([O:10][CH3:11])=[CH:6][CH:7]=[CH:8][CH:9]=1.Cl.[NH2:14]O>O.C(O)C>[CH3:11][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:3]=[N:14][OH:1]

Participants

6

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 141489N-[(2-methoxyphenyl)methylidene]hydroxylamineYield 117.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Add sodium hydroxide (8.50 g, 220 mmol) in water (150 mL) to a solution of o-anisaldehyde (25.0 g, 180 mmol) and hydroxylamine hydrochloride (15.4 g, 220 mmol) in ethanol (150 mL) and water (150 mL) at room temperature and stir the mixture for 3 hours. Acidify the mixture to pH 6 with 1 N HCl solution and collect the solids by vacuum filtration to provide 2-methoxybenzaldehyde oxime (32.0 g, 99%).

Workup

  1. customAcidify the mixture to pH 6 with 1 N HCl solution and collect the solids
  2. filtrationby vacuum filtration

Sources & evidence

ORD record
ord-73e312b0e4784bfb9c0cc2ba7bb1ec63
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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